organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 4| April 2011| Pages o962-o963

A second monoclinic polymorph of N-(di­ethyl­amino­thio­carbon­yl)-N′-phenyl­benzamidine

aCICECO, Departamento de Química, Faculdade de Ciências, Universidade do Aveiro, 3810-193 Aveiro, Portugal, bREQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre, 687, P-4169_007 Porto, Portugal, cCentro de Investigação em Química, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre 687, P-4169_007 Porto, Portugal, and dDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland
*Correspondence e-mail: jnlow111@gmail.com

(Received 5 March 2011; accepted 20 March 2011; online 26 March 2011)

The asymmetric unit of the title compound, C18H21N3S, contains five mol­ecules. The equivalent bond distances in the five mol­ecules are in excellent agreement, the r.m.s. fit being within 0.007 Å. The five mol­ecules are linked into a chain consisting of alternating pseudo-enanti­omers by N—H⋯S hydrogen bonds supplemented by weak C—H⋯π inter­actions. The action of a glide plane links the asymmetric unit into an extended chain. A polymorph of the title compound with one mol­ecule in the asymmetric unit was reported by Braun et al. [Cryst. Res. Technol. (1988), 23, 35–39].

Related literature

For the structure of the first polymorph, see: Braun et al. (1988[Braun, U., Sieler, J., Richter, R., Leba, I. & Golic, L. (1988). Cryst. Res. Technol. 23, 35-39.]). For graph-set analysis, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, I. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). Preparative details can be found in Beyer et al. (1984[Beyer, L., Hartung, J. & Widera, R. (1984). Tetrahedron, 40, 405-412.]).

[Scheme 1]

Experimental

Crystal data
  • C18H21N3S

  • Mr = 311.44

  • Monoclinic, P 21 /c

  • a = 21.2894 (8) Å

  • b = 18.8015 (7) Å

  • c = 27.1792 (10) Å

  • β = 128.584 (2)°

  • V = 8504.1 (5) Å3

  • Z = 20

  • Mo Kα radiation

  • μ = 0.19 mm−1

  • T = 150 K

  • 0.20 × 0.06 × 0.03 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.963, Tmax = 0.994

  • 54002 measured reflections

  • 17402 independent reflections

  • 9835 reflections with I > 2σ(I)

  • Rint = 0.053

Refinement
  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 0.142

  • S = 1.01

  • 17398 reflections

  • 1001 parameters

  • H-atom parameters constrained

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2, Cg4, Cg5, Cg8 and Cg10 are the centroids of the C121–C126, C221–C226, C321–C326, C421–C426 and C521–C526 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
N11—H11⋯S24 0.86 2.62 3.440 (2) 159
N21—H21⋯S34 0.86 2.60 3.407 (2) 157
N31—H31⋯S44 0.86 2.64 3.459 (2) 161
N41—H41⋯S54 0.86 2.62 3.416 (2) 155
N51—H51⋯S14i 0.86 2.62 3.431 (2) 157
C26—H26BCg2 0.99 2.91 3.594 (4) 127
C36—H36ACg4 0.99 2.86 3.575 (4) 130
C46—H46BCg6 0.99 2.84 3.549 (4) 129
C56—H56ACg8 0.99 2.89 3.566 (4) 126
C16—H16ACg10ii 0.99 2.86 3.552 (4) 128
Symmetry codes: (i) [x+2, -y+{\script{1\over 2}}, z+{\script{3\over 2}}]; (ii) [x-2, -y-{\script{1\over 2}}, z-{\script{5\over 2}}].

Data collection: APEX2 and SMART (Bruker, 2004[Bruker (2004). APEX2, SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT (Bruker, 2004[Bruker (2004). APEX2, SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and OSCAIL (McArdle et al., 2004[McArdle, P., Gilligan, K., Cunningham, D., Dark, R. & Mahon, M. (2004). CrystEngComm, 6, 303-309.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

As part of an investigation into the thermochemical properties of benzamidines a search of the CSD, (Allen, 2002) produced the structural details of C18H21N3S with the code GIDHEG which crystallized in P21/n with one molecule in the asymmetric unit. This structure was published by Braun et al., 1988, but data acquisition was made at room temperature and it was found to have an ethyl group with urealistic bond lengths and hydrogen atoms on the terminal methyl group were missing. It was thus decided to carry out a new structural determination at 150 K to locate this ethyl group more accurately in order to allow the comparison of the solid state structure with that obtained from gas phase ab initio calculations. The low temperature structure crystallizes in P21/c with cell volume of 8504.1 (5) Å3 close to five times that for GIDHEG, 1754.0 (5) Å3 and with five molecules in the asymmetric unit. The five independent molecules are shown in Figures 1 - 5.

Equivalent bond distances among the five molecules are in excellent agreement. The r.m.s. fit is within 0.007 Å (Spek, 2009). The five molecules in the asymmetric unit are linked into a chain by N—H···S hydrogen bonds, this chain is supplemented by the action of weak C—H···π interactions. Action of a glide plane links the asymmetric unit into an extended C6 chain, Bernstein et al., 1995, Figure 6.

Figures 1 - 5 show that molecules 1, 3, and 5 are alike and molecules 2 and 4 are alike. The r.m.s. fits of their orthogonal coordinates are obtained from PLATON (Spek, 2003). These pairwise r.m.s. fits are for molecules 1 and 3, 0.202 Å; for molecules 1 and 5, 0.178 Å; for molecules 3 and 5, 0.121 Å and for molecules 2 and 4, 0.142 Å. By contrast, the pairwise r.m.s. fits between molecules in sets 1,3,5 and 2,4 range from 3.808 to 3.900 Å. The only significant differences between the sets are in the conformation of the ethyl group labeled Cx51—Cx52 and in the rotational disposition of H atoms in some of the methyl groups. When molecules 2 and 4 are inverted they map onto molecules 1, 3, and 5 except for the above-mentioned ethyl group. Thus the chain is one of alternating pseudo-enantiomers.

Related literature top

For the structure of the first polymorph, see: Braun et al. (1988). For graph-set analysis, see: Bernstein et al. (1995). For a description of the Cambridge Structural Database, see: Allen (2002). Preparation details can be found in Beyer et al. (1984).

Experimental top

The synthesis of the title compound was performed as described in detail elsewhere, Beyer et al. (1984). PureN-(diethylaminothiocarbonyl)benzimide chloride (available through the reaction of equimolar amounts of bis(N',N'-diethyl-N-benzoylthioureato) nickel (II) and thionyl chloride in dried THF) reacts with ammonia or primary or secondary amines, in acetone. In the presence of proton trapping reagents (excess of ammonia or an equimolar amount on triethylamine) and after removing of the precipitated triethylamine hydrochloride and successive recrystallization from ethanol, the respective N-thiocarbamoylbenzamidine was yielded as pale yellow crystals.

Refinement top

Molecule (1) crystallized in the monoclinic system; space group P21/c with five N—H···S hydrogen bonded molecules in the asymmetric unit. A consequence of this is that the centre-of-gravity of residues 4 and 5 do not lie within the unit cell. H atoms were treated as riding atoms with C—H(aromatic), 0.95 Å, C—H2(alphatic), 0.99 Å, with Uiso = 1.2Ueq(C) and C—H3 (methyl), 0.98 Å, with Uiso = 1.5Ueq(C), H atoms attached to N atoms were located on a difference map, the bond length was initially fixed to 0.860 (1)Å then in the final cycles of refinement allowed to ride on the parent atom with Uiso = 1.2Ueq(N).

Low angle reflections obscured or partially obscured by the beamstop were omitted.

Computing details top

Data collection: APEX2 and SMART (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and OSCAIL (McArdle et al., 2004); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick 2008).

Figures top
[Figure 1] Fig. 1. A view of molecule 1 with our numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A view of molecule 2 with our numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 3] Fig. 3. A view of molecule 3 with our numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 4] Fig. 4. A view of molecule 4 with our numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 5] Fig. 5. A view of molecule 5 with our numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 6] Fig. 6. A steroscopic view of the chain formed by the N–H···S hydrogen bonds. Hydrogen atoms not involved in the hydrogen bonding are omitted for the sake of clarity.
3,3-diethyl-1-[phenyl(phenylamino)methylidene]thiourea top
Crystal data top
C18H21N3SF(000) = 3320
Mr = 311.44Dx = 1.216 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 21.2894 (8) ÅCell parameters from 558 reflections
b = 18.8015 (7) Åθ = 3.5–26.3°
c = 27.1792 (10) ŵ = 0.19 mm1
β = 128.584 (2)°T = 150 K
V = 8504.1 (5) Å3Plate, yellow
Z = 200.20 × 0.06 × 0.03 mm
Data collection top
Bruker SMART APEX
diffractometer
17402 independent reflections
Radiation source: fine-focus sealed tube9835 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
Detector resolution: 8.33 pixels mm-1θmax = 26.4°, θmin = 1.2°
ω scansh = 2626
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
k = 1923
Tmin = 0.963, Tmax = 0.994l = 3334
54002 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0532P)2 + 1.4021P]
where P = (Fo2 + 2Fc2)/3
17398 reflections(Δ/σ)max = 0.002
1001 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C18H21N3SV = 8504.1 (5) Å3
Mr = 311.44Z = 20
Monoclinic, P21/cMo Kα radiation
a = 21.2894 (8) ŵ = 0.19 mm1
b = 18.8015 (7) ÅT = 150 K
c = 27.1792 (10) Å0.20 × 0.06 × 0.03 mm
β = 128.584 (2)°
Data collection top
Bruker SMART APEX
diffractometer
17402 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
9835 reflections with I > 2σ(I)
Tmin = 0.963, Tmax = 0.994Rint = 0.053
54002 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.142H-atom parameters constrained
S = 1.01Δρmax = 0.34 e Å3
17398 reflectionsΔρmin = 0.29 e Å3
1001 parameters
Special details top

Experimental. Data for C18H21N3S: found 102 w(C)=69.24, 102 w(H)=6.56, 102 w(N)=13.60, 102 w(S)=10.58, calculated 102 w(C)=69.42, 102 w(H)=6.80, 102 w(N)=13.49, 102 w(S)=10.29

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S140.23152 (4)0.22025 (3)0.17728 (3)0.02237 (16)
N110.02123 (12)0.17913 (10)0.34861 (10)0.0198 (5)
H110.05960.20880.37270.024*
N130.09015 (12)0.15087 (10)0.24855 (10)0.0205 (5)
N150.16587 (12)0.13186 (10)0.14303 (10)0.0219 (5)
C120.04052 (15)0.19866 (12)0.28844 (12)0.0175 (6)
C140.15869 (15)0.16731 (11)0.18921 (12)0.0180 (6)
C160.23483 (16)0.14413 (14)0.07668 (13)0.0280 (6)
H16A0.28360.15200.07300.034*
H16B0.24380.10130.05190.034*
C170.22199 (17)0.20757 (15)0.04975 (14)0.0364 (7)
H17A0.26820.21280.00510.055*
H17B0.17310.20050.05410.055*
H17C0.21630.25060.07260.055*
C1110.03899 (16)0.10834 (12)0.37206 (12)0.0200 (6)
C1120.11730 (16)0.08396 (13)0.40673 (13)0.0268 (6)
H1120.15820.11470.41480.032*
C1130.13615 (17)0.01545 (13)0.42952 (13)0.0327 (7)
H1130.19000.00080.45300.039*
C1140.07749 (18)0.03008 (13)0.41861 (14)0.0322 (7)
H1140.09060.07740.43420.039*
C1150.00069 (18)0.00528 (13)0.38444 (13)0.0303 (7)
H1150.04130.03590.37690.036*
C1160.02042 (16)0.06343 (12)0.36115 (12)0.0229 (6)
H1160.07420.07980.33780.028*
C1210.03988 (15)0.27481 (12)0.27319 (12)0.0195 (6)
C1220.04437 (16)0.29136 (13)0.22116 (13)0.0263 (6)
H1220.05030.25440.19470.032*
C1230.04029 (16)0.36125 (13)0.20777 (13)0.0316 (7)
H1230.04270.37210.17250.038*
C1240.03274 (16)0.41535 (14)0.24531 (14)0.0332 (7)
H1240.03010.46340.23580.040*
C1250.02897 (16)0.39982 (13)0.29668 (13)0.0287 (7)
H1250.02420.43720.32230.034*
C1260.03208 (15)0.32944 (12)0.31115 (13)0.0231 (6)
H1260.02890.31880.34680.028*
C1510.10461 (15)0.07888 (13)0.15722 (13)0.0291 (7)
H15A0.12900.04740.12020.035*
H15B0.09040.04900.19290.035*
C1520.02819 (16)0.11010 (14)0.17348 (14)0.0363 (7)
H15C0.00540.07180.17670.054*
H15D0.00120.13520.21380.054*
H15E0.04170.14350.14050.054*
S240.17634 (4)0.27346 (3)0.47670 (3)0.02079 (16)
N210.42915 (12)0.30005 (10)0.64607 (10)0.0211 (5)
H210.46290.26780.67130.025*
N230.32595 (12)0.32552 (10)0.54203 (10)0.0197 (5)
N250.25155 (12)0.32914 (10)0.43525 (10)0.0198 (5)
C220.36825 (15)0.27907 (12)0.58633 (13)0.0194 (6)
C240.25506 (15)0.30905 (11)0.48411 (12)0.0168 (5)
C260.17791 (15)0.32437 (13)0.37021 (12)0.0261 (6)
H26A0.17590.36460.34580.031*
H26B0.13090.32820.36940.031*
C270.17323 (16)0.25506 (14)0.33968 (13)0.0359 (7)
H27A0.12510.25510.29540.054*
H27B0.17050.21520.36160.054*
H27C0.22110.25000.34230.054*
C2110.44753 (15)0.37149 (12)0.66763 (12)0.0201 (6)
C2120.52721 (16)0.39308 (13)0.70694 (13)0.0279 (7)
H2120.56830.36090.71750.033*
C2130.54674 (18)0.46140 (14)0.73072 (14)0.0359 (7)
H2130.60140.47600.75750.043*
C2140.48745 (19)0.50886 (13)0.71601 (14)0.0326 (7)
H2140.50110.55580.73250.039*
C2150.40839 (18)0.48707 (13)0.67718 (13)0.0301 (7)
H2150.36760.51940.66710.036*
C2160.38750 (16)0.41883 (12)0.65263 (12)0.0244 (6)
H2160.33280.40440.62580.029*
C2210.35905 (15)0.20031 (12)0.57676 (13)0.0233 (6)
C2220.35586 (16)0.16999 (14)0.52872 (13)0.0319 (7)
H2220.35830.19930.50150.038*
C2230.34902 (18)0.09671 (16)0.52042 (15)0.0460 (9)
H2230.34750.07580.48790.055*
C2240.34440 (18)0.05451 (15)0.55948 (16)0.0494 (10)
H2240.33910.00450.55340.059*
C2250.34739 (17)0.08392 (14)0.60681 (15)0.0422 (8)
H2250.34390.05420.63330.051*
C2260.35553 (16)0.15713 (13)0.61652 (14)0.0303 (7)
H2260.35870.17740.65000.036*
C2510.32204 (16)0.35829 (13)0.44386 (13)0.0283 (6)
H25A0.31820.34670.40650.034*
H25B0.37140.33570.48100.034*
C2520.32810 (19)0.43781 (14)0.45297 (16)0.0462 (9)
H25C0.37230.45600.45440.069*
H25D0.33830.44910.49260.069*
H25E0.27760.46000.41790.069*
S340.57027 (4)0.20604 (3)0.77842 (3)0.02182 (16)
N310.82249 (12)0.16993 (9)0.94887 (10)0.0199 (5)
H310.85840.20140.97310.024*
N330.71349 (12)0.13984 (9)0.84771 (10)0.0187 (5)
N350.63691 (12)0.12304 (10)0.74181 (10)0.0190 (5)
C320.76082 (15)0.18831 (12)0.88835 (12)0.0175 (6)
C340.64369 (15)0.15580 (11)0.78852 (12)0.0164 (5)
C360.56655 (15)0.13427 (13)0.67604 (12)0.0240 (6)
H36A0.51840.14090.67350.029*
H36B0.55780.09150.65120.029*
C370.57675 (16)0.19867 (14)0.64800 (13)0.0319 (7)
H37A0.52910.20400.60390.048*
H37B0.62430.19230.65040.048*
H37C0.58350.24130.67160.048*
C3110.84020 (15)0.10053 (12)0.97507 (12)0.0186 (6)
C3120.91956 (16)0.07851 (13)1.01483 (13)0.0274 (6)
H3120.96070.10911.02330.033*
C3130.93886 (17)0.01171 (13)1.04232 (13)0.0331 (7)
H3130.99340.00321.06960.040*
C3140.87961 (18)0.03343 (13)1.03053 (13)0.0314 (7)
H3140.89300.07921.04930.038*
C3150.80036 (17)0.01083 (13)0.99084 (13)0.0268 (6)
H3150.75920.04160.98230.032*
C3160.78034 (16)0.05582 (12)0.96349 (12)0.0228 (6)
H3160.72590.07100.93690.027*
C3210.75888 (14)0.26532 (12)0.87418 (12)0.0184 (6)
C3220.75293 (15)0.28526 (12)0.82203 (13)0.0247 (6)
H3220.74720.24990.79450.030*
C3230.75536 (16)0.35619 (13)0.81015 (14)0.0317 (7)
H3230.75190.36950.77480.038*
C3240.76285 (17)0.40776 (13)0.84963 (14)0.0331 (7)
H3240.76440.45650.84130.040*
C3250.76810 (16)0.38887 (13)0.90082 (14)0.0298 (7)
H3250.77270.42470.92750.036*
C3260.76675 (15)0.31776 (12)0.91388 (13)0.0232 (6)
H3260.77120.30490.94970.028*
C3510.70025 (15)0.07513 (12)0.75451 (13)0.0235 (6)
H35A0.67690.04440.71720.028*
H35B0.71730.04380.79020.028*
C3520.77462 (16)0.11171 (13)0.76987 (14)0.0303 (7)
H35C0.80920.07630.77090.045*
H35D0.80430.13490.81100.045*
H35E0.75820.14740.73760.045*
S440.97103 (4)0.27165 (3)1.07600 (3)0.02064 (16)
N411.22665 (12)0.30294 (10)1.24426 (10)0.0205 (5)
H411.26410.27291.26890.025*
N431.11834 (13)0.32832 (10)1.14204 (10)0.0199 (5)
N451.04558 (12)0.33060 (10)1.03541 (10)0.0213 (5)
C421.16571 (15)0.28189 (12)1.18444 (12)0.0186 (6)
C441.04862 (15)0.31032 (11)1.08374 (12)0.0179 (5)
C460.97333 (16)0.32224 (14)0.97023 (13)0.0310 (7)
H46A0.97040.36150.94460.037*
H46B0.92540.32520.96830.037*
C470.97268 (17)0.25186 (16)0.94288 (14)0.0434 (8)
H47A0.92470.24910.89860.065*
H47B0.97200.21280.96640.065*
H47C1.02090.24810.94590.065*
C4111.24352 (15)0.37451 (12)1.26575 (12)0.0197 (6)
C4121.32171 (16)0.39872 (13)1.30205 (13)0.0280 (7)
H4121.36340.36771.31190.034*
C4131.33974 (18)0.46792 (13)1.32419 (14)0.0344 (7)
H4131.39370.48431.34920.041*
C4141.27925 (19)0.51327 (13)1.30987 (14)0.0352 (7)
H4141.29150.56101.32440.042*
C4151.20113 (18)0.48899 (13)1.27444 (13)0.0297 (7)
H4151.15980.51991.26530.036*
C4161.18272 (16)0.41976 (13)1.25222 (12)0.0244 (6)
H4161.12890.40321.22790.029*
C4211.16223 (15)0.20419 (12)1.17216 (12)0.0202 (6)
C4221.15931 (16)0.18123 (14)1.12229 (13)0.0304 (7)
H4221.15950.21511.09640.036*
C4231.15607 (17)0.10929 (15)1.10993 (14)0.0390 (8)
H4231.15470.09381.07600.047*
C4241.15479 (16)0.06015 (14)1.14698 (15)0.0376 (8)
H4241.15190.01081.13820.045*
C4251.15765 (16)0.08220 (13)1.19641 (14)0.0322 (7)
H4251.15690.04811.22180.039*
C4261.16169 (15)0.15433 (12)1.20946 (13)0.0239 (6)
H4261.16410.16941.24400.029*
C4511.11588 (15)0.36182 (13)1.04462 (13)0.0272 (6)
H45A1.11240.35161.00720.033*
H45B1.16550.33931.08160.033*
C4521.12087 (19)0.44068 (14)1.05463 (15)0.0457 (9)
H45C1.16450.46011.05590.069*
H45D1.13140.45081.09460.069*
H45E1.06990.46271.02000.069*
S541.37598 (4)0.21402 (3)1.37768 (3)0.02200 (16)
N511.62793 (12)0.18011 (10)1.54716 (10)0.0209 (5)
H511.66170.21311.57110.025*
N531.52037 (12)0.14940 (10)1.44597 (10)0.0189 (5)
N551.44223 (12)0.13268 (10)1.34005 (10)0.0211 (5)
C521.56515 (15)0.19807 (12)1.48708 (12)0.0182 (6)
C541.45012 (15)0.16539 (11)1.38743 (12)0.0183 (6)
C561.37164 (16)0.14475 (13)1.27431 (12)0.0270 (6)
H56A1.32340.14941.27180.032*
H56B1.36380.10311.24870.032*
C571.38034 (17)0.21090 (14)1.24744 (13)0.0334 (7)
H57A1.33260.21661.20340.050*
H57B1.42810.20651.24990.050*
H57C1.38600.25251.27170.050*
C5111.64861 (16)0.11016 (12)1.57227 (12)0.0205 (6)
C5121.72888 (16)0.09059 (13)1.61213 (13)0.0276 (7)
H5121.76880.12341.62110.033*
C5131.75108 (18)0.02355 (14)1.63886 (14)0.0334 (7)
H5131.80620.01041.66600.040*
C5141.69336 (18)0.02463 (13)1.62629 (13)0.0319 (7)
H5141.70860.07081.64440.038*
C5151.61325 (18)0.00462 (13)1.58699 (13)0.0290 (7)
H5151.57340.03721.57840.035*
C5161.59073 (16)0.06252 (12)1.56013 (12)0.0232 (6)
H5161.53570.07591.53340.028*
C5211.55848 (15)0.27605 (12)1.47388 (13)0.0239 (6)
C5221.55626 (16)0.29979 (13)1.42436 (13)0.0319 (7)
H5221.55830.26671.39900.038*
C5231.55099 (18)0.37207 (15)1.41215 (15)0.0465 (9)
H5231.55030.38871.37880.056*
C5241.54682 (19)0.41941 (15)1.44827 (17)0.0539 (10)
H5241.54270.46891.43950.065*
C5251.54845 (18)0.39633 (14)1.49707 (17)0.0474 (9)
H5251.54550.42981.52180.057*
C5261.55436 (16)0.32412 (13)1.51028 (14)0.0320 (7)
H5261.55560.30801.54400.038*
C5511.50538 (15)0.08427 (13)1.35181 (13)0.0286 (7)
H55A1.48150.05341.31450.034*
H55B1.52380.05321.38790.034*
C5521.57743 (17)0.12203 (14)1.36545 (15)0.0399 (8)
H55C1.61280.08721.36690.060*
H55D1.60680.14651.40610.060*
H55E1.55940.15691.33220.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S140.0212 (4)0.0243 (3)0.0205 (4)0.0059 (3)0.0124 (4)0.0011 (3)
N110.0176 (12)0.0184 (10)0.0149 (13)0.0041 (9)0.0059 (11)0.0017 (9)
N130.0183 (12)0.0188 (10)0.0169 (13)0.0023 (9)0.0074 (11)0.0007 (10)
N150.0171 (12)0.0265 (11)0.0166 (13)0.0003 (9)0.0077 (11)0.0046 (10)
C120.0159 (14)0.0202 (12)0.0177 (16)0.0007 (11)0.0111 (14)0.0005 (11)
C140.0177 (14)0.0168 (12)0.0181 (15)0.0026 (10)0.0105 (13)0.0008 (11)
C160.0211 (16)0.0409 (15)0.0165 (16)0.0009 (13)0.0091 (14)0.0053 (13)
C170.0312 (18)0.0553 (19)0.0253 (19)0.0032 (14)0.0189 (17)0.0048 (15)
C1110.0236 (15)0.0195 (12)0.0125 (15)0.0005 (11)0.0091 (14)0.0002 (11)
C1120.0229 (16)0.0241 (13)0.0268 (18)0.0010 (12)0.0122 (15)0.0007 (12)
C1130.0288 (18)0.0296 (15)0.0274 (18)0.0057 (13)0.0116 (16)0.0040 (13)
C1140.044 (2)0.0189 (13)0.0251 (18)0.0015 (13)0.0176 (17)0.0014 (12)
C1150.0396 (19)0.0246 (14)0.0238 (18)0.0133 (13)0.0183 (16)0.0056 (13)
C1160.0217 (15)0.0268 (13)0.0143 (16)0.0032 (12)0.0083 (14)0.0015 (12)
C1210.0133 (14)0.0208 (12)0.0199 (16)0.0001 (11)0.0082 (14)0.0024 (11)
C1220.0253 (16)0.0290 (14)0.0227 (17)0.0033 (12)0.0140 (15)0.0007 (12)
C1230.0320 (18)0.0342 (15)0.0237 (18)0.0069 (13)0.0149 (16)0.0052 (13)
C1240.0271 (17)0.0225 (14)0.038 (2)0.0017 (12)0.0145 (17)0.0085 (14)
C1250.0220 (16)0.0214 (13)0.0303 (18)0.0014 (12)0.0102 (15)0.0041 (13)
C1260.0215 (16)0.0225 (13)0.0215 (17)0.0002 (11)0.0115 (15)0.0002 (12)
C1510.0262 (16)0.0313 (14)0.0275 (18)0.0025 (12)0.0156 (15)0.0061 (13)
C1520.0322 (18)0.0380 (16)0.045 (2)0.0072 (14)0.0268 (18)0.0022 (15)
S240.0193 (4)0.0225 (3)0.0207 (4)0.0038 (3)0.0126 (4)0.0009 (3)
N210.0218 (13)0.0174 (10)0.0156 (13)0.0047 (9)0.0074 (12)0.0001 (9)
N230.0168 (12)0.0231 (11)0.0139 (13)0.0022 (9)0.0070 (11)0.0000 (10)
N250.0173 (12)0.0248 (11)0.0146 (13)0.0035 (9)0.0087 (11)0.0005 (9)
C220.0193 (15)0.0225 (13)0.0189 (16)0.0004 (11)0.0132 (14)0.0009 (12)
C240.0166 (14)0.0119 (11)0.0188 (15)0.0024 (10)0.0095 (13)0.0016 (11)
C260.0193 (15)0.0385 (15)0.0154 (16)0.0025 (12)0.0083 (14)0.0021 (13)
C270.0231 (17)0.0593 (19)0.0276 (19)0.0092 (14)0.0169 (16)0.0143 (15)
C2110.0233 (15)0.0198 (12)0.0157 (15)0.0010 (11)0.0115 (14)0.0003 (11)
C2120.0199 (16)0.0263 (14)0.0270 (18)0.0044 (12)0.0095 (15)0.0010 (13)
C2130.0301 (18)0.0314 (15)0.035 (2)0.0094 (14)0.0146 (17)0.0055 (14)
C2140.047 (2)0.0205 (13)0.0246 (18)0.0003 (14)0.0193 (17)0.0002 (13)
C2150.0395 (19)0.0251 (14)0.0212 (17)0.0133 (13)0.0167 (16)0.0046 (13)
C2160.0236 (16)0.0247 (13)0.0185 (16)0.0046 (12)0.0101 (14)0.0011 (12)
C2210.0149 (15)0.0226 (13)0.0198 (16)0.0048 (11)0.0046 (14)0.0006 (12)
C2220.0252 (17)0.0319 (15)0.0248 (18)0.0078 (13)0.0088 (15)0.0050 (13)
C2230.0336 (19)0.0400 (18)0.034 (2)0.0128 (15)0.0062 (18)0.0141 (16)
C2240.032 (2)0.0232 (15)0.046 (2)0.0049 (14)0.0011 (19)0.0068 (16)
C2250.0308 (19)0.0250 (15)0.041 (2)0.0012 (13)0.0081 (18)0.0055 (15)
C2260.0247 (17)0.0241 (14)0.0298 (19)0.0001 (12)0.0110 (16)0.0000 (13)
C2510.0242 (16)0.0390 (15)0.0239 (17)0.0081 (13)0.0161 (15)0.0028 (13)
C2520.059 (2)0.0419 (17)0.052 (2)0.0242 (16)0.041 (2)0.0113 (16)
S340.0202 (4)0.0231 (3)0.0210 (4)0.0039 (3)0.0122 (4)0.0009 (3)
N310.0212 (13)0.0172 (10)0.0153 (13)0.0048 (9)0.0085 (12)0.0005 (9)
N330.0183 (12)0.0177 (10)0.0167 (13)0.0019 (9)0.0092 (11)0.0002 (9)
N350.0163 (12)0.0209 (10)0.0155 (13)0.0027 (9)0.0078 (11)0.0011 (9)
C320.0173 (14)0.0206 (12)0.0170 (16)0.0004 (11)0.0118 (14)0.0006 (12)
C340.0165 (14)0.0137 (11)0.0157 (15)0.0014 (10)0.0083 (13)0.0028 (11)
C360.0205 (15)0.0312 (14)0.0139 (16)0.0025 (12)0.0075 (14)0.0021 (12)
C370.0288 (18)0.0429 (16)0.0234 (18)0.0079 (13)0.0160 (16)0.0072 (14)
C3110.0215 (15)0.0188 (12)0.0126 (15)0.0006 (11)0.0091 (13)0.0005 (11)
C3120.0242 (16)0.0247 (13)0.0272 (18)0.0040 (12)0.0130 (15)0.0001 (13)
C3130.0274 (17)0.0285 (14)0.0237 (18)0.0051 (13)0.0063 (15)0.0040 (13)
C3140.0432 (19)0.0193 (13)0.0196 (17)0.0018 (13)0.0137 (16)0.0026 (12)
C3150.0352 (18)0.0233 (13)0.0202 (17)0.0099 (12)0.0165 (16)0.0030 (12)
C3160.0235 (16)0.0279 (14)0.0172 (16)0.0035 (12)0.0129 (14)0.0021 (12)
C3210.0113 (14)0.0173 (12)0.0193 (16)0.0023 (10)0.0060 (13)0.0013 (11)
C3220.0230 (16)0.0234 (13)0.0242 (17)0.0020 (11)0.0130 (15)0.0003 (12)
C3230.0307 (18)0.0277 (14)0.0295 (19)0.0055 (13)0.0153 (16)0.0059 (14)
C3240.0306 (18)0.0191 (13)0.035 (2)0.0044 (12)0.0136 (17)0.0054 (13)
C3250.0222 (16)0.0196 (13)0.039 (2)0.0023 (12)0.0150 (16)0.0063 (13)
C3260.0188 (15)0.0225 (13)0.0248 (17)0.0019 (11)0.0120 (14)0.0019 (12)
C3510.0252 (16)0.0201 (12)0.0235 (17)0.0041 (11)0.0143 (15)0.0017 (12)
C3520.0310 (17)0.0284 (14)0.041 (2)0.0085 (12)0.0270 (17)0.0058 (13)
S440.0200 (4)0.0220 (3)0.0196 (4)0.0041 (3)0.0122 (4)0.0013 (3)
N410.0162 (12)0.0208 (10)0.0156 (13)0.0044 (9)0.0056 (11)0.0017 (9)
N430.0184 (12)0.0216 (10)0.0141 (13)0.0030 (9)0.0074 (11)0.0002 (10)
N450.0155 (12)0.0303 (11)0.0140 (13)0.0038 (9)0.0072 (11)0.0019 (10)
C420.0145 (14)0.0238 (13)0.0169 (16)0.0010 (11)0.0095 (14)0.0010 (12)
C440.0178 (14)0.0153 (11)0.0169 (15)0.0021 (11)0.0090 (13)0.0005 (11)
C460.0205 (16)0.0521 (17)0.0138 (16)0.0064 (14)0.0075 (14)0.0040 (14)
C470.0300 (18)0.075 (2)0.031 (2)0.0165 (16)0.0216 (17)0.0232 (17)
C4110.0240 (15)0.0178 (12)0.0151 (15)0.0021 (11)0.0112 (14)0.0025 (11)
C4120.0233 (16)0.0252 (14)0.0299 (18)0.0033 (12)0.0138 (16)0.0022 (13)
C4130.0333 (18)0.0261 (14)0.0311 (19)0.0056 (13)0.0139 (17)0.0018 (14)
C4140.051 (2)0.0197 (13)0.0280 (19)0.0029 (14)0.0208 (18)0.0025 (13)
C4150.0372 (19)0.0280 (14)0.0201 (17)0.0145 (13)0.0161 (16)0.0051 (13)
C4160.0218 (16)0.0302 (14)0.0180 (16)0.0077 (12)0.0107 (14)0.0040 (12)
C4210.0122 (14)0.0224 (13)0.0166 (16)0.0033 (11)0.0044 (13)0.0007 (11)
C4220.0278 (17)0.0364 (15)0.0204 (17)0.0086 (13)0.0118 (15)0.0015 (13)
C4230.0326 (19)0.0402 (17)0.0292 (19)0.0143 (14)0.0120 (17)0.0085 (15)
C4240.0236 (17)0.0244 (14)0.039 (2)0.0065 (13)0.0067 (16)0.0087 (14)
C4250.0241 (17)0.0242 (14)0.038 (2)0.0025 (12)0.0142 (16)0.0002 (14)
C4260.0178 (15)0.0232 (13)0.0229 (17)0.0004 (11)0.0088 (14)0.0028 (12)
C4510.0223 (15)0.0377 (15)0.0207 (16)0.0086 (12)0.0129 (14)0.0023 (13)
C4520.052 (2)0.0405 (17)0.051 (2)0.0165 (16)0.035 (2)0.0024 (16)
S540.0187 (4)0.0230 (3)0.0223 (4)0.0039 (3)0.0118 (4)0.0011 (3)
N510.0211 (13)0.0168 (10)0.0164 (13)0.0082 (9)0.0076 (12)0.0021 (9)
N530.0150 (12)0.0198 (10)0.0178 (13)0.0005 (9)0.0082 (11)0.0013 (10)
N550.0161 (12)0.0261 (11)0.0180 (13)0.0019 (9)0.0091 (11)0.0013 (10)
C520.0138 (14)0.0216 (12)0.0144 (15)0.0010 (11)0.0064 (13)0.0002 (11)
C540.0178 (14)0.0138 (11)0.0217 (16)0.0035 (10)0.0115 (14)0.0003 (11)
C560.0198 (15)0.0365 (15)0.0182 (16)0.0005 (12)0.0087 (14)0.0019 (13)
C570.0275 (17)0.0496 (17)0.0245 (18)0.0039 (14)0.0168 (16)0.0068 (14)
C5110.0269 (16)0.0184 (12)0.0132 (15)0.0018 (11)0.0111 (14)0.0003 (11)
C5120.0251 (17)0.0255 (14)0.0277 (18)0.0051 (12)0.0142 (16)0.0001 (13)
C5130.0280 (17)0.0333 (15)0.0264 (18)0.0045 (13)0.0108 (16)0.0021 (14)
C5140.045 (2)0.0194 (13)0.0246 (18)0.0004 (13)0.0187 (17)0.0029 (13)
C5150.0382 (19)0.0245 (13)0.0221 (17)0.0108 (13)0.0177 (16)0.0006 (12)
C5160.0229 (15)0.0269 (13)0.0150 (15)0.0050 (12)0.0094 (14)0.0000 (12)
C5210.0150 (15)0.0200 (12)0.0247 (17)0.0033 (11)0.0066 (14)0.0007 (12)
C5220.0246 (17)0.0307 (15)0.0244 (18)0.0071 (13)0.0074 (15)0.0056 (13)
C5230.035 (2)0.0355 (17)0.034 (2)0.0143 (15)0.0043 (18)0.0121 (16)
C5240.035 (2)0.0198 (15)0.054 (3)0.0068 (14)0.002 (2)0.0091 (17)
C5250.0291 (19)0.0245 (15)0.058 (3)0.0017 (14)0.0123 (19)0.0097 (16)
C5260.0204 (16)0.0259 (14)0.035 (2)0.0020 (12)0.0100 (16)0.0039 (14)
C5510.0217 (16)0.0354 (15)0.0270 (18)0.0049 (12)0.0144 (15)0.0019 (13)
C5520.0364 (19)0.0389 (16)0.050 (2)0.0078 (14)0.0297 (19)0.0088 (16)
Geometric parameters (Å, º) top
S14—C141.695 (2)C314—C3151.386 (4)
N11—C121.362 (3)C314—H3140.9500
N11—C1111.421 (3)C315—C3161.382 (3)
N11—H110.8601C315—H3150.9500
N13—C121.292 (3)C316—H3160.9500
N13—C141.375 (3)C321—C3261.392 (3)
N15—C141.343 (3)C321—C3221.394 (3)
N15—C161.469 (3)C322—C3231.381 (3)
N15—C1511.488 (3)C322—H3220.9500
C12—C1211.493 (3)C323—C3241.380 (4)
C16—C171.511 (3)C323—H3230.9500
C16—H16A0.9900C324—C3251.371 (4)
C16—H16B0.9900C324—H3240.9500
C17—H17A0.9800C325—C3261.388 (3)
C17—H17B0.9800C325—H3250.9500
C17—H17C0.9800C326—H3260.9500
C111—C1121.385 (3)C351—C3521.526 (3)
C111—C1161.390 (3)C351—H35A0.9900
C112—C1131.376 (3)C351—H35B0.9900
C112—H1120.9500C352—H35C0.9800
C113—C1141.385 (4)C352—H35D0.9800
C113—H1130.9500C352—H35E0.9800
C114—C1151.386 (4)S44—C441.694 (2)
C114—H1140.9500N41—C421.361 (3)
C115—C1161.384 (3)N41—C4111.421 (3)
C115—H1150.9500N41—H410.8592
C116—H1160.9500N43—C421.287 (3)
C121—C1261.390 (3)N43—C441.377 (3)
C121—C1221.392 (3)N45—C441.330 (3)
C122—C1231.381 (3)N45—C461.460 (3)
C122—H1220.9500N45—C4511.476 (3)
C123—C1241.377 (4)C42—C4211.490 (3)
C123—H1230.9500C46—C471.513 (4)
C124—C1251.379 (4)C46—H46A0.9900
C124—H1240.9500C46—H46B0.9900
C125—C1261.394 (3)C47—H47A0.9800
C125—H1250.9500C47—H47B0.9800
C126—H1260.9500C47—H47C0.9800
C151—C1521.513 (3)C411—C4121.379 (3)
C151—H15A0.9900C411—C4161.393 (3)
C151—H15B0.9900C412—C4131.384 (3)
C152—H15C0.9800C412—H4120.9500
C152—H15D0.9800C413—C4141.382 (4)
C152—H15E0.9800C413—H4130.9500
S24—C241.696 (2)C414—C4151.380 (4)
N21—C221.359 (3)C414—H4140.9500
N21—C2111.419 (3)C415—C4161.385 (3)
N21—H210.8603C415—H4150.9500
N23—C221.293 (3)C416—H4160.9500
N23—C241.374 (3)C421—C4261.386 (3)
N25—C241.337 (3)C421—C4221.387 (3)
N25—C261.461 (3)C422—C4231.385 (4)
N25—C2511.473 (3)C422—H4220.9500
C22—C2211.495 (3)C423—C4241.379 (4)
C26—C271.515 (3)C423—H4230.9500
C26—H26A0.9900C424—C4251.371 (4)
C26—H26B0.9900C424—H4240.9500
C27—H27A0.9800C425—C4261.391 (3)
C27—H27B0.9800C425—H4250.9500
C27—H27C0.9800C426—H4260.9500
C211—C2121.387 (3)C451—C4521.499 (4)
C211—C2161.393 (3)C451—H45A0.9900
C212—C2131.380 (3)C451—H45B0.9900
C212—H2120.9500C452—H45C0.9800
C213—C2141.386 (4)C452—H45D0.9800
C213—H2130.9500C452—H45E0.9800
C214—C2151.378 (4)S54—C541.696 (2)
C214—H2140.9500N51—C521.358 (3)
C215—C2161.385 (3)N51—C5111.420 (3)
C215—H2150.9500N51—H510.8601
C216—H2160.9500N53—C521.291 (3)
C221—C2221.387 (3)N53—C541.375 (3)
C221—C2261.391 (4)N55—C541.340 (3)
C222—C2231.389 (4)N55—C561.467 (3)
C222—H2220.9500N55—C5511.484 (3)
C223—C2241.377 (4)C52—C5211.495 (3)
C223—H2230.9500C56—C571.511 (3)
C224—C2251.365 (4)C56—H56A0.9900
C224—H2240.9500C56—H56B0.9900
C225—C2261.392 (3)C57—H57A0.9800
C225—H2250.9500C57—H57B0.9800
C226—H2260.9500C57—H57C0.9800
C251—C2521.508 (3)C511—C5121.386 (3)
C251—H25A0.9900C511—C5161.386 (3)
C251—H25B0.9900C512—C5131.383 (3)
C252—H25C0.9800C512—H5120.9500
C252—H25D0.9800C513—C5141.387 (4)
C252—H25E0.9800C513—H5130.9500
S34—C341.696 (2)C514—C5151.385 (4)
N31—C321.362 (3)C514—H5140.9500
N31—C3111.420 (3)C515—C5161.386 (3)
N31—H310.8601C515—H5150.9500
N33—C321.295 (3)C516—H5160.9500
N33—C341.380 (3)C521—C5261.382 (4)
N35—C341.335 (3)C521—C5221.391 (4)
N35—C361.464 (3)C522—C5231.387 (4)
N35—C3511.473 (3)C522—H5220.9500
C32—C3211.492 (3)C523—C5241.368 (5)
C36—C371.517 (3)C523—H5230.9500
C36—H36A0.9900C524—C5251.375 (5)
C36—H36B0.9900C524—H5240.9500
C37—H37A0.9800C525—C5261.390 (4)
C37—H37B0.9800C525—H5250.9500
C37—H37C0.9800C526—H5260.9500
C311—C3121.384 (3)C551—C5521.512 (3)
C311—C3161.389 (3)C551—H55A0.9900
C312—C3131.386 (3)C551—H55B0.9900
C312—H3120.9500C552—H55C0.9800
C313—C3141.382 (4)C552—H55D0.9800
C313—H3130.9500C552—H55E0.9800
C12—N11—C111125.3 (2)C316—C315—C314120.9 (2)
C12—N11—H11119.2C316—C315—H315119.5
C111—N11—H11113.8C314—C315—H315119.5
C12—N13—C14122.8 (2)C315—C316—C311119.7 (2)
C14—N15—C16120.9 (2)C315—C316—H316120.2
C14—N15—C151121.3 (2)C311—C316—H316120.2
C16—N15—C151117.8 (2)C326—C321—C322119.2 (2)
N13—C12—N11119.4 (2)C326—C321—C32121.1 (2)
N13—C12—C121125.3 (2)C322—C321—C32119.6 (2)
N11—C12—C121115.0 (2)C323—C322—C321120.3 (2)
N15—C14—N13113.8 (2)C323—C322—H322119.8
N15—C14—S14123.7 (2)C321—C322—H322119.8
N13—C14—S14122.10 (18)C324—C323—C322120.0 (3)
N15—C16—C17112.0 (2)C324—C323—H323120.0
N15—C16—H16A109.2C322—C323—H323120.0
C17—C16—H16A109.2C325—C324—C323120.3 (2)
N15—C16—H16B109.2C325—C324—H324119.9
C17—C16—H16B109.2C323—C324—H324119.9
H16A—C16—H16B107.9C324—C325—C326120.5 (2)
C16—C17—H17A109.5C324—C325—H325119.8
C16—C17—H17B109.5C326—C325—H325119.8
H17A—C17—H17B109.5C325—C326—C321119.7 (3)
C16—C17—H17C109.5C325—C326—H326120.1
H17A—C17—H17C109.5C321—C326—H326120.1
H17B—C17—H17C109.5N35—C351—C352115.50 (19)
C112—C111—C116119.6 (2)N35—C351—H35A108.4
C112—C111—N11119.1 (2)C352—C351—H35A108.4
C116—C111—N11121.4 (2)N35—C351—H35B108.4
C113—C112—C111120.4 (2)C352—C351—H35B108.4
C113—C112—H112119.8H35A—C351—H35B107.5
C111—C112—H112119.8C351—C352—H35C109.5
C112—C113—C114120.8 (3)C351—C352—H35D109.5
C112—C113—H113119.6H35C—C352—H35D109.5
C114—C113—H113119.6C351—C352—H35E109.5
C113—C114—C115118.7 (2)H35C—C352—H35E109.5
C113—C114—H114120.6H35D—C352—H35E109.5
C115—C114—H114120.6C42—N41—C411125.1 (2)
C116—C115—C114121.0 (2)C42—N41—H41118.0
C116—C115—H115119.5C411—N41—H41115.4
C114—C115—H115119.5C42—N43—C44123.0 (2)
C115—C116—C111119.6 (2)C44—N45—C46122.2 (2)
C115—C116—H116120.2C44—N45—C451121.8 (2)
C111—C116—H116120.2C46—N45—C451116.0 (2)
C126—C121—C122119.3 (2)N43—C42—N41120.2 (2)
C126—C121—C12121.3 (2)N43—C42—C421124.2 (2)
C122—C121—C12119.3 (2)N41—C42—C421115.5 (2)
C123—C122—C121120.3 (2)N45—C44—N43114.8 (2)
C123—C122—H122119.8N45—C44—S44123.9 (2)
C121—C122—H122119.8N43—C44—S44121.09 (18)
C124—C123—C122120.3 (3)N45—C46—C47111.7 (2)
C124—C123—H123119.8N45—C46—H46A109.3
C122—C123—H123119.8C47—C46—H46A109.3
C123—C124—C125120.0 (2)N45—C46—H46B109.3
C123—C124—H124120.0C47—C46—H46B109.3
C125—C124—H124120.0H46A—C46—H46B107.9
C124—C125—C126120.2 (2)C46—C47—H47A109.5
C124—C125—H125119.9C46—C47—H47B109.5
C126—C125—H125119.9H47A—C47—H47B109.5
C121—C126—C125119.8 (2)C46—C47—H47C109.5
C121—C126—H126120.1H47A—C47—H47C109.5
C125—C126—H126120.1H47B—C47—H47C109.5
N15—C151—C152115.1 (2)C412—C411—C416119.7 (2)
N15—C151—H15A108.5C412—C411—N41119.3 (2)
C152—C151—H15A108.5C416—C411—N41121.0 (2)
N15—C151—H15B108.5C411—C412—C413120.3 (2)
C152—C151—H15B108.5C411—C412—H412119.8
H15A—C151—H15B107.5C413—C412—H412119.8
C151—C152—H15C109.5C414—C413—C412120.0 (3)
C151—C152—H15D109.5C414—C413—H413120.0
H15C—C152—H15D109.5C412—C413—H413120.0
C151—C152—H15E109.5C415—C414—C413119.9 (2)
H15C—C152—H15E109.5C415—C414—H414120.1
H15D—C152—H15E109.5C413—C414—H414120.1
C22—N21—C211125.4 (2)C414—C415—C416120.4 (2)
C22—N21—H21116.6C414—C415—H415119.8
C211—N21—H21117.4C416—C415—H415119.8
C22—N23—C24123.0 (2)C415—C416—C411119.7 (3)
C24—N25—C26122.5 (2)C415—C416—H416120.2
C24—N25—C251121.8 (2)C411—C416—H416120.2
C26—N25—C251115.7 (2)C426—C421—C422119.2 (2)
N23—C22—N21120.5 (2)C426—C421—C42121.4 (2)
N23—C22—C221124.6 (2)C422—C421—C42119.3 (2)
N21—C22—C221114.8 (2)C423—C422—C421120.4 (3)
N25—C24—N23114.5 (2)C423—C422—H422119.8
N25—C24—S24123.7 (2)C421—C422—H422119.8
N23—C24—S24121.53 (18)C424—C423—C422119.8 (3)
N25—C26—C27111.7 (2)C424—C423—H423120.1
N25—C26—H26A109.3C422—C423—H423120.1
C27—C26—H26A109.3C425—C424—C423120.3 (3)
N25—C26—H26B109.3C425—C424—H424119.9
C27—C26—H26B109.3C423—C424—H424119.9
H26A—C26—H26B107.9C424—C425—C426120.2 (3)
C26—C27—H27A109.5C424—C425—H425119.9
C26—C27—H27B109.5C426—C425—H425119.9
H27A—C27—H27B109.5C421—C426—C425120.0 (3)
C26—C27—H27C109.5C421—C426—H426120.0
H27A—C27—H27C109.5C425—C426—H426120.0
H27B—C27—H27C109.5N45—C451—C452111.9 (2)
C212—C211—C216119.8 (2)N45—C451—H45A109.2
C212—C211—N21119.0 (2)C452—C451—H45A109.2
C216—C211—N21121.2 (2)N45—C451—H45B109.2
C213—C212—C211120.0 (2)C452—C451—H45B109.2
C213—C212—H212120.0H45A—C451—H45B107.9
C211—C212—H212120.0C451—C452—H45C109.5
C212—C213—C214120.7 (3)C451—C452—H45D109.5
C212—C213—H213119.7H45C—C452—H45D109.5
C214—C213—H213119.7C451—C452—H45E109.5
C215—C214—C213119.2 (2)H45C—C452—H45E109.5
C215—C214—H214120.4H45D—C452—H45E109.5
C213—C214—H214120.4C52—N51—C511125.9 (2)
C214—C215—C216121.1 (3)C52—N51—H51117.5
C214—C215—H215119.5C511—N51—H51116.2
C216—C215—H215119.5C52—N53—C54122.0 (2)
C215—C216—C211119.4 (3)C54—N55—C56121.2 (2)
C215—C216—H216120.3C54—N55—C551121.4 (2)
C211—C216—H216120.3C56—N55—C551117.4 (2)
C222—C221—C226119.8 (2)N53—C52—N51120.4 (2)
C222—C221—C22119.7 (2)N53—C52—C521125.4 (2)
C226—C221—C22120.5 (2)N51—C52—C521114.0 (2)
C221—C222—C223119.9 (3)N55—C54—N53113.9 (2)
C221—C222—H222120.0N55—C54—S54123.4 (2)
C223—C222—H222120.0N53—C54—S54122.23 (19)
C224—C223—C222119.8 (3)N55—C56—C57112.0 (2)
C224—C223—H223120.1N55—C56—H56A109.2
C222—C223—H223120.1C57—C56—H56A109.2
C225—C224—C223120.6 (3)N55—C56—H56B109.2
C225—C224—H224119.7C57—C56—H56B109.2
C223—C224—H224119.7H56A—C56—H56B107.9
C224—C225—C226120.4 (3)C56—C57—H57A109.5
C224—C225—H225119.8C56—C57—H57B109.5
C226—C225—H225119.8H57A—C57—H57B109.5
C221—C226—C225119.4 (3)C56—C57—H57C109.5
C221—C226—H226120.3H57A—C57—H57C109.5
C225—C226—H226120.3H57B—C57—H57C109.5
N25—C251—C252111.7 (2)C512—C511—C516119.6 (2)
N25—C251—H25A109.3C512—C511—N51118.9 (2)
C252—C251—H25A109.3C516—C511—N51121.4 (2)
N25—C251—H25B109.3C513—C512—C511120.2 (2)
C252—C251—H25B109.3C513—C512—H512119.9
H25A—C251—H25B107.9C511—C512—H512119.9
C251—C252—H25C109.5C512—C513—C514120.4 (3)
C251—C252—H25D109.5C512—C513—H513119.8
H25C—C252—H25D109.5C514—C513—H513119.8
C251—C252—H25E109.5C515—C514—C513119.2 (2)
H25C—C252—H25E109.5C515—C514—H514120.4
H25D—C252—H25E109.5C513—C514—H514120.4
C32—N31—C311126.4 (2)C514—C515—C516120.6 (2)
C32—N31—H31118.5C514—C515—H515119.7
C311—N31—H31114.6C516—C515—H515119.7
C32—N33—C34122.7 (2)C515—C516—C511119.9 (3)
C34—N35—C36121.06 (19)C515—C516—H516120.0
C34—N35—C351121.3 (2)C511—C516—H516120.0
C36—N35—C351117.66 (19)C526—C521—C522120.3 (2)
N33—C32—N31120.2 (2)C526—C521—C52120.6 (2)
N33—C32—C321125.5 (2)C522—C521—C52119.2 (2)
N31—C32—C321114.1 (2)C523—C522—C521119.7 (3)
N35—C34—N33114.0 (2)C523—C522—H522120.2
N35—C34—S34124.1 (2)C521—C522—H522120.2
N33—C34—S34121.57 (18)C524—C523—C522119.8 (3)
N35—C36—C37111.7 (2)C524—C523—H523120.1
N35—C36—H36A109.3C522—C523—H523120.1
C37—C36—H36A109.3C523—C524—C525120.8 (3)
N35—C36—H36B109.3C523—C524—H524119.6
C37—C36—H36B109.3C525—C524—H524119.6
H36A—C36—H36B107.9C524—C525—C526120.1 (3)
C36—C37—H37A109.5C524—C525—H525120.0
C36—C37—H37B109.5C526—C525—H525120.0
H37A—C37—H37B109.5C521—C526—C525119.3 (3)
C36—C37—H37C109.5C521—C526—H526120.3
H37A—C37—H37C109.5C525—C526—H526120.3
H37B—C37—H37C109.5N55—C551—C552114.1 (2)
C312—C311—C316119.8 (2)N55—C551—H55A108.7
C312—C311—N31118.6 (2)C552—C551—H55A108.7
C316—C311—N31121.6 (2)N55—C551—H55B108.7
C311—C312—C313119.9 (2)C552—C551—H55B108.7
C311—C312—H312120.0H55A—C551—H55B107.6
C313—C312—H312120.0C551—C552—H55C109.5
C314—C313—C312120.7 (3)C551—C552—H55D109.5
C314—C313—H313119.7H55C—C552—H55D109.5
C312—C313—H313119.7C551—C552—H55E109.5
C313—C314—C315119.0 (2)H55C—C552—H55E109.5
C313—C314—H314120.5H55D—C552—H55E109.5
C315—C314—H314120.5
C14—N13—C12—N11172.7 (2)C313—C314—C315—C3160.3 (4)
C14—N13—C12—C12113.1 (4)C314—C315—C316—C3111.0 (4)
C111—N11—C12—N132.7 (3)C312—C311—C316—C3151.2 (4)
C111—N11—C12—C121172.0 (2)N31—C311—C316—C315178.8 (2)
C16—N15—C14—N13178.8 (2)N33—C32—C321—C326137.4 (3)
C151—N15—C14—N131.3 (3)N31—C32—C321—C32647.7 (3)
C16—N15—C14—S148.0 (3)N33—C32—C321—C32245.7 (3)
C151—N15—C14—S14171.87 (17)N31—C32—C321—C322129.3 (2)
C12—N13—C14—N15127.4 (2)C326—C321—C322—C3230.4 (4)
C12—N13—C14—S1459.2 (3)C32—C321—C322—C323176.6 (2)
C14—N15—C16—C1784.2 (3)C321—C322—C323—C3240.7 (4)
C151—N15—C16—C1796.0 (3)C322—C323—C324—C3250.2 (4)
C12—N11—C111—C112131.9 (3)C323—C324—C325—C3260.7 (4)
C12—N11—C111—C11648.4 (3)C324—C325—C326—C3210.9 (4)
C116—C111—C112—C1130.9 (4)C322—C321—C326—C3250.4 (4)
N11—C111—C112—C113179.4 (2)C32—C321—C326—C325177.3 (2)
C111—C112—C113—C1140.4 (4)C34—N35—C351—C35277.3 (3)
C112—C113—C114—C1150.2 (4)C36—N35—C351—C352102.0 (3)
C113—C114—C115—C1160.4 (4)C44—N43—C42—N41169.5 (2)
C114—C115—C116—C1110.1 (4)C44—N43—C42—C42114.3 (4)
C112—C111—C116—C1150.7 (4)C411—N41—C42—N430.7 (4)
N11—C111—C116—C115179.6 (2)C411—N41—C42—C421177.1 (2)
N13—C12—C121—C126134.9 (3)C46—N45—C44—N43173.9 (2)
N11—C12—C121—C12650.7 (3)C451—N45—C44—N437.3 (3)
N13—C12—C121—C12247.3 (3)C46—N45—C44—S441.1 (3)
N11—C12—C121—C122127.1 (2)C451—N45—C44—S44177.82 (17)
C126—C121—C122—C1230.6 (4)C42—N43—C44—N45119.8 (2)
C12—C121—C122—C123177.1 (2)C42—N43—C44—S4465.1 (3)
C121—C122—C123—C1240.8 (4)C44—N45—C46—C4791.2 (3)
C122—C123—C124—C1250.2 (4)C451—N45—C46—C4787.7 (3)
C123—C124—C125—C1260.6 (4)C42—N41—C411—C412133.9 (3)
C122—C121—C126—C1250.1 (4)C42—N41—C411—C41647.9 (3)
C12—C121—C126—C125177.8 (2)C416—C411—C412—C4131.0 (4)
C124—C125—C126—C1210.7 (4)N41—C411—C412—C413179.2 (2)
C14—N15—C151—C15278.0 (3)C411—C412—C413—C4140.1 (4)
C16—N15—C151—C152102.2 (3)C412—C413—C414—C4151.2 (4)
C24—N23—C22—N21167.5 (2)C413—C414—C415—C4161.1 (4)
C24—N23—C22—C22116.4 (4)C414—C415—C416—C4110.0 (4)
C211—N21—C22—N236.7 (4)C412—C411—C416—C4151.1 (4)
C211—N21—C22—C221176.8 (2)N41—C411—C416—C415179.2 (2)
C26—N25—C24—N23172.16 (19)N43—C42—C421—C426130.8 (3)
C251—N25—C24—N237.2 (3)N41—C42—C421—C42652.9 (3)
C26—N25—C24—S242.1 (3)N43—C42—C421—C42249.1 (3)
C251—N25—C24—S24178.55 (17)N41—C42—C421—C422127.2 (3)
C22—N23—C24—N25127.5 (2)C426—C421—C422—C4230.1 (4)
C22—N23—C24—S2458.1 (3)C42—C421—C422—C423180.0 (2)
C24—N25—C26—C2793.4 (3)C421—C422—C423—C4240.8 (4)
C251—N25—C26—C2787.2 (2)C422—C423—C424—C4250.8 (4)
C22—N21—C211—C212137.0 (3)C423—C424—C425—C4260.1 (4)
C22—N21—C211—C21646.3 (3)C422—C421—C426—C4250.5 (4)
C216—C211—C212—C2130.4 (4)C42—C421—C426—C425179.4 (2)
N21—C211—C212—C213177.1 (2)C424—C425—C426—C4210.5 (4)
C211—C212—C213—C2140.3 (4)C44—N45—C451—C45286.6 (3)
C212—C213—C214—C2150.0 (4)C46—N45—C451—C45294.5 (3)
C213—C214—C215—C2160.2 (4)C54—N53—C52—N51170.8 (2)
C214—C215—C216—C2110.2 (4)C54—N53—C52—C52113.9 (4)
C212—C211—C216—C2150.2 (4)C511—N51—C52—N533.8 (4)
N21—C211—C216—C215176.8 (2)C511—N51—C52—C521179.6 (2)
N23—C22—C221—C22248.2 (4)C56—N55—C54—N53178.78 (19)
N21—C22—C221—C222128.1 (3)C551—N55—C54—N530.3 (3)
N23—C22—C221—C226133.3 (3)C56—N55—C54—S548.4 (3)
N21—C22—C221—C22650.4 (3)C551—N55—C54—S54173.14 (17)
C226—C221—C222—C2230.1 (4)C52—N53—C54—N55132.6 (2)
C22—C221—C222—C223178.6 (2)C52—N53—C54—S5454.5 (3)
C221—C222—C223—C2240.8 (4)C54—N55—C56—C5783.7 (3)
C222—C223—C224—C2250.8 (5)C551—N55—C56—C5794.8 (3)
C223—C224—C225—C2260.3 (5)C52—N51—C511—C512138.6 (3)
C222—C221—C226—C2251.1 (4)C52—N51—C511—C51644.5 (4)
C22—C221—C226—C225179.7 (2)C516—C511—C512—C5131.0 (4)
C224—C225—C226—C2211.2 (4)N51—C511—C512—C513178.0 (2)
C24—N25—C251—C25288.3 (3)C511—C512—C513—C5140.3 (4)
C26—N25—C251—C25291.1 (3)C512—C513—C514—C5150.5 (4)
C34—N33—C32—N31170.6 (2)C513—C514—C515—C5160.4 (4)
C34—N33—C32—C32114.7 (4)C514—C515—C516—C5110.3 (4)
C311—N31—C32—N333.1 (4)C512—C511—C516—C5151.1 (4)
C311—N31—C32—C321178.4 (2)N51—C511—C516—C515178.0 (2)
C36—N35—C34—N33179.83 (19)N53—C52—C521—C526129.5 (3)
C351—N35—C34—N330.6 (3)N51—C52—C521—C52655.0 (3)
C36—N35—C34—S346.2 (3)N53—C52—C521—C52250.4 (4)
C351—N35—C34—S34174.57 (16)N51—C52—C521—C522125.1 (3)
C32—N33—C34—N35128.7 (2)C526—C521—C522—C5230.9 (4)
C32—N33—C34—S3457.2 (3)C52—C521—C522—C523179.3 (2)
C34—N35—C36—C3786.7 (3)C521—C522—C523—C5241.0 (4)
C351—N35—C36—C3792.6 (2)C522—C523—C524—C5250.5 (5)
C32—N31—C311—C312137.7 (3)C523—C524—C525—C5260.0 (5)
C32—N31—C311—C31644.7 (3)C522—C521—C526—C5250.4 (4)
C316—C311—C312—C3130.8 (4)C52—C521—C526—C525179.8 (2)
N31—C311—C312—C313178.4 (2)C524—C525—C526—C5210.1 (4)
C311—C312—C313—C3140.0 (4)C54—N55—C551—C55277.8 (3)
C312—C313—C314—C3150.2 (4)C56—N55—C551—C552100.7 (3)
Hydrogen-bond geometry (Å, º) top
Cg2, Cg4, Cg5, Cg8 and Cg10 are the centroids of the C121–C126, C221–C226, C321–C326, C421–C426 and C521–C526 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N11—H11···S240.862.623.440 (2)159
N21—H21···S340.862.603.407 (2)157
N31—H31···S440.862.643.459 (2)161
N41—H41···S540.862.623.416 (2)155
N51—H51···S14i0.862.623.431 (2)157
C26—H26B···Cg20.992.913.594 (4)127
C36—H36A···Cg40.992.863.575 (4)130
C46—H46B···Cg60.992.843.549 (4)129
C56—H56A···Cg80.992.893.566 (4)126
C16—H16A···Cg10ii0.992.863.552 (4)128
Symmetry codes: (i) x+2, y+1/2, z+3/2; (ii) x2, y1/2, z5/2.

Experimental details

Crystal data
Chemical formulaC18H21N3S
Mr311.44
Crystal system, space groupMonoclinic, P21/c
Temperature (K)150
a, b, c (Å)21.2894 (8), 18.8015 (7), 27.1792 (10)
β (°) 128.584 (2)
V3)8504.1 (5)
Z20
Radiation typeMo Kα
µ (mm1)0.19
Crystal size (mm)0.20 × 0.06 × 0.03
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2004)
Tmin, Tmax0.963, 0.994
No. of measured, independent and
observed [I > 2σ(I)] reflections
54002, 17402, 9835
Rint0.053
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.142, 1.01
No. of reflections17398
No. of parameters1001
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.29

Computer programs: APEX2 and SMART (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and OSCAIL (McArdle et al., 2004), PLATON (Spek, 2009), SHELXL97 (Sheldrick 2008).

Hydrogen-bond geometry (Å, º) top
Cg2, Cg4, Cg5, Cg8 and Cg10 are the centroids of the C121–C126, C221–C226, C321–C326, C421–C426 and C521–C526 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N11—H11···S240.862.623.440 (2)159
N21—H21···S340.862.603.407 (2)157
N31—H31···S440.862.643.459 (2)161
N41—H41···S540.862.623.416 (2)155
N51—H51···S14i0.862.623.431 (2)157
C26—H26B···Cg20.992.913.594 (4)127
C36—H36A···Cg40.992.863.575 (4)130
C46—H46B···Cg60.992.843.549 (4)129
C56—H56A···Cg80.992.893.566 (4)126
C16—H16A···Cg10ii0.992.863.552 (4)128
Symmetry codes: (i) x+2, y+1/2, z+3/2; (ii) x2, y1/2, z5/2.
 

Acknowledgements

BS acknowledges the FCT and the European Social Fund (ESF) under the third Community Support Framework (CSF) for the award of a post-doctoral research grant (SFRH/BPD/38637/2007).

References

First citationAllen, F. H. (2002). Acta Cryst. B58, 380–388.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationBernstein, J., Davis, R. E., Shimoni, I. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
First citationBeyer, L., Hartung, J. & Widera, R. (1984). Tetrahedron, 40, 405–412.  CrossRef CAS Google Scholar
First citationBraun, U., Sieler, J., Richter, R., Leba, I. & Golic, L. (1988). Cryst. Res. Technol. 23, 35–39.  CrossRef CAS Google Scholar
First citationBruker (2004). APEX2, SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationMcArdle, P., Gilligan, K., Cunningham, D., Dark, R. & Mahon, M. (2004). CrystEngComm, 6, 303–309.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 4| April 2011| Pages o962-o963
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds